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17 O chemical shifts and deuterium isotope effects on 13 C chemical shifts of intramolecularly hydrogen‐bonded compounds
Author(s) -
Kozerski Lech,
Kawȩcki Robert,
Krajewski Piotr,
Kwiecień Bru,
Boykin David W.,
Bolvig Simon,
Hansen Poul Erik
Publication year - 1998
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/(sici)1097-458x(199812)36:12<921::aid-omr392>3.0.co;2-r
Subject(s) - chemical shift , chemistry , intramolecular force , deuterium , steric effects , kinetic isotope effect , hydrogen bond , hydrogen , chemical bond , deuterium nmr , computational chemistry , photochemistry , molecule , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , physics , quantum mechanics
17 O chemical shifts were measured in 40 enaminesactivated in the β‐position by C=O, COO,NO 2 , SO and SO 2 groups. Data for theoxygen‐containing series of o ‐hydroxyacylaromatics are also included for comparison. Intramolecular hydrogenbonding in the enamines is discussed in terms of the acceptor anddonor groups and the separating link. 17 O chemical shifts,the two‐bond deuterium isotope shifts on C‐α 13 C shifts and 1 H NH or OH chemical shifts arecorrelated to show the interrelations of these parameters inelucidating intramolecular hydrogen bonds and their strength in a widevariety of compounds. 17 O chemical shifts inopen‐chain compounds are shown to reflect intramolecularhydrogen bonding by a change to lower frequency whereas forfive‐membered rings steric effects cause higher frequencychemical shifts. © 1998 John Wiley & Sons, Ltd.